CN1527871A

CN1527871A - Light-emitting device and aromatic compound

Info

Publication number: CN1527871A
Application number: CNA028139909A
Authority: CN
Inventors: Ҳ; 五十岚达也; 邱雪鹏
Original assignee: Fujifilm Corp
Current assignee: UDC Ireland Ltd
Priority date: 2001-07-11
Filing date: 2002-07-10
Publication date: 2004-09-08
Anticipated expiration: 2022-07-10
Also published as: CN1302087C; US20040232409A1; TW575540B; US7733012B2; EP1412450B1; WO2003007658A8; US7517592B2; WO2003007658A3; US20080152948A1; EP1412450A2; JP2004535051A; WO2003007658A2; JP4515760B2; US20080233430A1; AU2002317506A1; ATE547499T1; KR100902524B1; KR20040028918A

Abstract

A light-emitting device comprising a pair of electrodes and a light-emitting layer or a plurality of organic layers comprising a light-emitting layer disposed therebetween, the light emitting layer or at least one of a plurality of organic layers comprising the light-emitting layer comprising at least one compound represented by the following general formula (1): wherein each of Ar<11>, Ar<12>, Ar<13>, Ar<14 >and Ar<15 >represents an aryl group or a heteroaryl group; Ar represents a benzene ring, a naphthalene ring; a phenanthrene ring or an anthracene ring; at least one of Ar, Ar<11>, Ar<12>, Ar<13>, Ar<14 >and Ar<15 >is a condensed aryl group, a condensed or uncondensed heteroaryl group or a group comprising a condensed aryl group or a condensed or uncondensed heteroaryl group; Ar<11>, Ar<12>, Ar<13>, Ar<14 >and Ar<15 >are not bonded to each other to form a ring; R<11 >represents a substituent; and n<11 >represents an integer of 0 or more.

Description

Luminaire and aromatic compound

Technical field

The present invention relates to a kind of luminaire that electric energy is transformed into light, particularly a kind of luminaire that is applicable to indicator elment, indicating meter, backlight, electrofax, lighting source, recording light source, exposure light source, reads light source, signal and sign, signboard, interior lighting, optical communication equipment or the like, and a kind of novel aromatic compound that can be used for this luminaire.

Background technology

In recent years people always active research and the exploitation various display equipments.Specifically, organic electroluminescent (EL) equipment is owing to only apply the light that less voltage just can send high brightness, so they receive sizable concern.For example, in Applied Physics Letters the 51st volume the 913rd page (1987) a kind of luminaire that the organic thin layer that provides by the vapor deposition organic compound is provided is disclosed.This luminaire has a kind of like this structure, wherein be arranged between the electrode, present the luminescent properties more excellent thus than the luminaire of traditional single layer structure as three (oxine acidic group) aluminium complexs (Alq) of electrically conductive material with as the amine compound of hole-conductive material form with laminate.

Carried out positive research and development in recent years so that organic el device is used for full-color display.For full-color display efficiently is provided, each color in reply blueness, green and the redness improves luminescent properties.For example, blue-light-emitting equipment is deficiency aspect purity of color, wearing quality, luminosity and luminous efficiency, and therefore needs to improve.In order to address these problems, to study the equipment (JP 11-12205 A etc.) that comprises aromatic fused ring compound, but still had a problem, that is exactly that the luminous efficiency of these luminaires is low, can not send the blue light of high color purity.In addition, in organic el device, also need to improve.

The purpose of this invention is to provide a kind of the have excellent characteristics of luminescence and the luminaire of wearing quality.

Another object of the present invention provides the aromatic compound that can be used for described luminaire of a kind of purity of color and wearing quality excellence.

Summary of the invention

For top purpose, the inventor furthers investigate, and found that, a kind of luminaire that comprises the aromatic compound with ad hoc structure has the excellent characteristics of luminescence and wearing quality.Finished the present invention based on this discovery.

Therefore, luminaire of the present invention comprises pair of electrodes and luminescent layer or between described electrode and comprise a plurality of organic layers of a luminescent layer, wherein said luminescent layer or comprise the compound that one deck at least in a plurality of organic layers of a luminescent layer comprises at least a general formula (1) representative:

Ar wherein ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵Represent aryl or heteroaryl separately; Ar represents phenyl ring, naphthalene nucleus, phenanthrene ring or anthracene nucleus; Ar, Ar ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵In at least one is fused-aryl, condenses or the heteroaryl of uncondensed or one comprise fused-aryl or condenses or the group of the heteroaryl of uncondensed; Ar ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵Do not link to each other each other and form ring; R ¹¹Represent a substituting group; And n ¹¹Represent 0 or bigger integer.

In general formula (1), Ar ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵In at least one is a pyrenyl.

In the superincumbent general formula (1), R ¹¹, Ar ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵In at least four fused-aryls or condense or the heteroaryl of uncondensed preferably, be more preferably fused-aryl, most preferably be phenanthryl or pyrenyl.

In the superincumbent general formula (1), R ¹¹, Ar ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵In at least one is selected from naphthyl, phenanthryl, anthryl, fluoranthene base, pyrenyl He perylene base, be more preferably naphthyl or phenanthryl.

The compound of general formula (1) representative is preferably luminous by singlet excited.

First preferred embodiment of general formula (1) is following general formula (2):

Ar wherein ²¹, Ar ²², Ar ²³, Ar ²⁴And Ar ²⁵Represent aryl or heteroaryl separately; Ar ²¹, Ar ²², Ar ²³, Ar ²⁴And Ar ²⁵In at least one is fused-aryl, condenses or the heteroaryl of uncondensed or one comprise fused-aryl or condenses or the group of the heteroaryl of uncondensed; Ar ²¹, Ar ²², Ar ²³, Ar ²⁴And Ar ²⁵Do not link to each other each other and form ring; R ²¹Represent a hydrogen atom or a substituting group.

In general formula (2), preferred Ar ²¹, Ar ²², Ar ²³And Ar ²⁴Be selected from phenyl, naphthyl, anthryl, phenanthryl and fluoranthene base separately; Ar ²⁵Be selected from phenyl, naphthyl, anthryl, phenanthryl, fluoranthene base, pyrenyl He perylene base; R ²¹Be selected from hydrogen atom, alkyl and aryl; Ar ²¹, Ar ²², Ar ²³, Ar ²⁴And Ar ²⁵In at least one is a fused-aryl; Ar ²¹, Ar ²², Ar ²³, Ar ²⁴And Ar ²⁵Do not link to each other each other and form ring.

In general formula (2), Ar ²¹, Ar ²², Ar ²³And Ar ²⁴More preferably be selected from phenyl, naphthyl and phenanthryl, most preferably phenyl separately.

In general formula (2), Ar ²⁵More preferably be selected from anthryl, phenanthryl, fluoranthene base, pyrenyl He perylene base.

In general formula (2), R ²¹More preferably be selected from hydrogen atom, phenyl and pyrenyl.

In the superincumbent general formula (2), R ²¹, Ar ²¹, Ar ²², Ar ²3, Ar ²⁴And Ar ²⁵In at least four fused-aryls or condense or the heteroaryl of uncondensed preferably, be more preferably fused-aryl, most preferably be phenanthryl or pyrenyl.

In the superincumbent general formula (2), Ar ²¹And Ar ²²Each is fused-aryl or condense or the heteroaryl of uncondensed naturally, is more preferably fused-aryl, most preferably is phenanthryl or pyrenyl.

In the superincumbent general formula (2), Ar ²¹And Ar ²⁴Fused-aryl or condense or the heteroaryl of uncondensed preferably is more preferably fused-aryl separately, most preferably is phenanthryl or pyrenyl.

In the superincumbent general formula (2), R ¹¹, Ar ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵In at least one is selected from naphthyl, phenanthryl, anthryl, fluoranthene base, pyrenyl He perylene base, be more preferably naphthyl or phenanthryl.

In the superincumbent general formula (2), preferred Ar ²¹And Ar ²³Each is fused-aryl naturally, and R ²¹, Ar ²², Ar ²⁴And Ar ²⁵Be selected from phenyl, naphthyl, phenanthryl, anthryl, fluoranthene base, pyrenyl He perylene base separately; More preferably Ar ²¹And Ar ²³Each is pyrenyl naturally, and R ²¹, Ar ²², Ar ²⁴And Ar ²⁵Be selected from phenyl, naphthyl and phenanthryl separately.

First preferred embodiment of general formula (2) is following general formula (5):

Ar wherein ⁵¹, Ar ⁵², Ar ⁵³And Ar ⁵⁴Represent aryl separately, R ⁵¹Represent a hydrogen atom or a substituting group, R ⁵²Represent a substituting group, and n ⁵¹It is the integer of 0-9.

In general formula (5), Ar ⁵¹, Ar ⁵², Ar ⁵³And Ar ⁵⁴Be preferably selected from phenyl, naphthyl, anthryl, phenanthryl and fluoranthene base, more preferably phenyl separately.

In general formula (5), R ⁵¹Be preferably selected from hydrogen atom, alkyl and aryl, more preferably be selected from hydrogen atom, phenyl and pyrenyl, most preferably phenyl or pyrenyl.

Second preferred embodiment of general formula (2) is following general formula (6):

Ar wherein ⁶¹, Ar ⁶², Ar ⁶³, Ar ⁶⁴, Ar ⁶⁵, Ar ⁶⁶, Ar ⁶⁷And Ar ⁶⁸Represent aryl or heteroaryl separately; R ⁶¹And R ⁶²Represent a hydrogen atom or a substituting group separately; R ⁶³, R ⁶⁴And R ⁶⁵Represent a substituting group separately; n ⁶¹And n ⁶²Each is the integer of 0-5 naturally; n ⁶³And n ⁶⁴Each is the integer of 0-4 naturally; And n ⁶⁵It is the integer of 0-8.

In general formula (6), Ar ⁶¹, Ar ⁶², Ar ⁶³, Ar ⁶⁴, Ar ⁶⁵, Ar ⁶⁶, Ar ⁶⁷And Ar ⁶⁸Be preferably selected from phenyl, naphthyl and phenanthryl separately.Specifically, R ⁶¹And R ⁶²Be preferably selected from hydrogen atom, phenyl and pyrenyl separately.n ⁶¹And n ⁶²Be preferably 0 or 1 separately.

Second preferred embodiment of general formula (1) is following general formula (3):

Ar wherein ³¹, Ar ³², Ar ³³, Ar ³⁴, Ar ³⁵, Ar ³⁶, Ar ³⁷And Ar ³⁸Represent aryl or heteroaryl separately; And Ar ³¹, Ar ³², Ar ³³, Ar ³⁴, Ar ³⁵, Ar ³⁶, Ar ³⁷And Ar ³⁸Do not link to each other each other and form ring.

In general formula (3), Ar ³¹, Ar ³², Ar ³³, Ar ³⁴, Ar ³⁵, Ar ³⁶, Ar ³⁷And Ar ³⁸Aryl preferably more preferably is selected from phenyl, naphthyl, anthryl, phenanthryl and pyrenyl, most preferably phenyl separately.

The 3rd preferred embodiment of general formula (1) is following general formula (4):

Ar wherein ⁴¹, Ar ⁴², Ar ⁴³, Ar ⁴⁴, Ar ⁴⁵, Ar ⁴⁶, Ar ⁴⁷, Ar ⁴⁸, Ar ⁴⁹And Ar ⁵⁰Represent aryl or heteroaryl separately; And Ar ⁴¹, Ar ⁴², Ar ⁴³, Ar ⁴⁴, Ar ⁴⁵, Ar ⁴⁶, Ar ⁴⁷, Ar ⁴⁸, Ar ⁴⁹And Ar ⁵⁰Do not link to each other each other and form ring.

In general formula (4), Ar ⁴¹, Ar ⁴², Ar ⁴³, Ar ⁴⁴, Ar ⁴⁵, Ar ⁴⁶, Ar ⁴⁷, Ar ⁴⁸, Ar ⁴⁹And Ar ⁵⁰Aryl preferably more preferably is selected from phenyl, naphthyl, anthryl, phenanthryl and pyrenyl, most preferably phenyl separately.

The compound of general formula (1) is more preferably represented by general formula (2) preferably by any expression in top general formula (2)-(4).

The content of compound in luminescent layer as luminescent material general formula (1) representative is preferably 0.1-100 quality %.

Be preferably 10-99.9 quality % as the compound of material of main part general formula (1) representative at luminescent layer or the content that comprises in one deck at least of a plurality of organic layers of luminescent layer.

In superincumbent luminescent layer and a plurality of organic layer that comprises top luminescent layer, at least one is luminescent layer preferably.

Superincumbent luminescent layer and comprise that at least one is preferably hole-conductive layer in a plurality of organic layers of top luminescent layer.

Top luminescent layer preferably includes at least a fluorescent chemicals.

Aromatic compound of the present invention is represented by general formula (5):

Ar wherein ⁵¹, Ar ⁵², Ar ⁵³And Ar ⁵⁴Represent aryl separately; R ⁵¹Represent a hydrogen atom or a substituting group; R ⁵²Represent a substituting group; And n ⁵¹It is the integer of 0-9.

The aromatic compound of general formula (5) representative is a preferred embodiment of the compound of general formula (2) representative, and it can be preferably used as the compound of general formula (1) representative.

Implement best mode of the present invention

Luminaire of the present invention comprises pair of electrodes and luminescent layer and between described electrode and comprise a plurality of organic layers of a luminescent layer.Described luminescent layer or comprise one deck at least in a plurality of organic layers of luminescent layer comprise at least a below the compound of general formula (1) expression.This paper back is referred to as " compound (1) " or " compound of the present invention " with the compound of any representative in general formula (1)-(6).

In general formula (1), Ar ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵Represent aryl or heteroaryl separately.The example of aryl comprises phenyl, naphthyl, anthryl, phenanthryl, fluoranthene base, pyrenyl, perylene base, Qu Ji, triphenylenyl, benzo anthryl, benzo phenanthryl etc.Wherein preferred phenyl, naphthyl, anthryl, phenanthryl, pyrenyl are with the perylene base.Condense or the example of the heteroaryl of uncondensed comprises pyridyl, quinolyl, quinoxalinyl, quinazolyl, acridyl, phenanthridinyl, phthalazinyl, phenanthroline base, triazinyl etc.Wherein preferred pyridyl, quinolyl and triazinyl.Ar ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵Can have a substituting group separately, this substituent example can with the described R in back ¹¹Those are identical.Ar ¹⁵, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵Aryl preferably separately.Ar ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵Do not link to each other each other and form ring.

In general formula (1), Ar represents phenyl ring, naphthalene nucleus, phenanthrene ring or anthracene nucleus.Ar is phenyl ring or naphthalene nucleus preferably, more preferably phenyl ring.

Ar, Ar ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵In at least one is fused-aryl or a group that comprises fused-aryl, for example naphthyl, phenanthryl, anthryl, pyrenyl, perylene base, fluoranthene base etc.; Or condense or the heteroaryl of uncondensed or one comprise and condenses or the group of the heteroaryl of uncondensed for example pyridyl, quinolyl, quinoxalinyl, quinazolyl, acridyl, phenanthridinyl, phthalazinyl, phenanthroline base, triazinyl etc.Ar, Ar ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵In at least one preferably fused-aryl or the group that comprises fused-aryl, more preferably a pyrenyl.The quantity of pyrenyl is preferably 2 or still less in the compound (1).Comprise fused-aryl or condense or the top group of the heteroaryl of uncondensed can or condense or the heteroaryl of uncondensed by fused-aryl, with compositions such as alkylidene group, arylidene, although it is preferred only by fused-aryl or condense or the heteroaryl of uncondensed is formed.

In general formula (1), R ¹¹Represent a substituting group.Substituent R ¹¹Example comprise alkyl, the quantity of its carbon atom is 1-30 preferably, more preferably 1-20,1-10 most preferably is such as methyl, ethyl, sec.-propyl, the tertiary butyl, n-octyl, positive decyl, n-hexadecyl, cyclopropyl, cyclopentyl and cyclohexyl; Alkenyl, the quantity of its carbon atom is 2-30 preferably, more preferably 2-20,2-10 most preferably is such as vinyl, allyl group, crotyl and 3-pentenyl; Alkynyl group, the quantity of its carbon atom is 2-30 preferably, more preferably 2-20,2-10 most preferably is such as proyl and 3-pentynyl; Aryl, the quantity of its carbon atom is 6-30 preferably, more preferably 6-20,6-12 most preferably is such as phenyl, p-methylphenyl, naphthyl and anthranilo; Amino, the quantity of its carbon atom is 0-30 preferably, more preferably 0-20,0-10 most preferably is such as amino, methylamino, dimethylamino, diethylamino, dibenzyl amino, diphenyl amino and xylyl amino; Alkoxyl group, the quantity of its carbon atom is 1-30 preferably, more preferably 1-20,1-10 most preferably is such as methoxyl group, oxyethyl group, butoxy and 2-ethyl hexyl oxy; Aryloxy, the quantity of its carbon atom is 6-30 preferably, more preferably 6-20,6-12 most preferably is such as phenoxy group, 1-naphthyloxy and 2-naphthyloxy; Heterocyclic oxy group, the quantity of its carbon atom is 1-30 preferably, more preferably 1-20,1-12 most preferably is such as pyridyloxy, pyrazine oxygen base, 2-pyrimidinyl oxy and quinoline oxy; Acyl group, the quantity of its carbon atom is 1-30 preferably, more preferably 1-20,1-12 most preferably is such as ethanoyl, benzoyl, formyl radical and valeryl; Alkoxy carbonyl, the quantity of its carbon atom is 2-30 preferably, more preferably 2-20,2-12 most preferably is such as methoxycarbonyl and ethoxy carbonyl; Aryloxycarbonyl, the quantity of its carbon atom is 7-30 preferably, more preferably 7-20,7-12 most preferably is such as phenyloxycarbonyl; Acyloxy, the quantity of its carbon atom is 2-30 preferably, more preferably 2-20,2-10 most preferably is such as acetoxyl group and benzoyloxy; Amido, the quantity of its carbon atom is 2-30 preferably, more preferably 2-20,2-10 most preferably is such as kharophen and benzamido; Alkoxycarbonyl amino, the quantity of its carbon atom is 2-30 preferably, more preferably 2-20,2-12 most preferably is such as methoxycarbonyl amino; Aryloxycarbonyl amino, the quantity of its carbon atom is 7-30 preferably, more preferably 7-20,7-12 most preferably is such as phenyloxycarbonyl amino; Sulfuryl amino, the quantity of its carbon atom is 1-30 preferably, more preferably 1-20,1-12 most preferably, the amino and benzenesulfonyl amino such as methylsulfonyl; Sulfamyl, the quantity of its carbon atom is 0-30 preferably, more preferably 0-20,0-12 most preferably is such as sulfamyl, methyl sulfamyl, dimethylamino alkylsulfonyl and phenyl sulfamoyl base; Formamyl, the quantity of its carbon atom is 1-30 preferably, more preferably 1-20,1-12 most preferably is such as formamyl, methylamino formyl radical, diethylamino formyl radical, phenyl amino formyl radical; Alkylthio, the quantity of its carbon atom is 1-30 preferably, more preferably 1-20,1-12 most preferably is such as methylthio group and ethylmercapto group; Arylthio, the quantity of its carbon atom is 6-30 preferably, more preferably 6-20,6-12 most preferably is such as thiophenyl; The heterocycle sulfenyl, the quantity of its carbon atom is 1-30 preferably, more preferably 1-20,1-12 most preferably is such as pyridyl sulfenyl, 2-benzimidazolyl-sulfenyl, 2-benzoxazolyl sulfenyl and 2-[4-morpholinodithio base sulfenyl; Alkylsulfonyl, the quantity of its carbon atom is 1-30 preferably, more preferably 1-20,1-12 most preferably is such as methylsulfonyl and tosyl group; Sulfinyl, the quantity of its carbon atom is 1-30 preferably, more preferably 1-20,1-12 most preferably is such as methanesulfinyl and benzenesulfinyl; The uride base, the quantity of its carbon atom is 1-30 preferably, more preferably 1-20,1-12 most preferably is such as uride base, methyl uride base and phenyl uride base; Phosphinylidyne amino, the quantity of its carbon atom is 1-30 preferably, more preferably 1-20,1-12 most preferably, the amino and phenyl phosphinylidyne amino such as the diethyl phosphinylidyne; Hydroxyl; Sulfydryl; Halogen atom such as fluorine atom, chlorine atom, bromine atoms and iodine atom; Cyano group; Sulfo group; Carboxyl; Nitro; The hydroxamic acid base; Sulfino; Diazanyl; Imino-; Contain nitrogen-atoms, Sauerstoffatom, sulphur atom etc. as heteroatomic heterocyclic radical, the quantity of its carbon atom is 1-30 preferably, more preferably 1-12 is such as imidazolyl, pyridyl, quinolyl, furfuryl group, thienyl, piperidyl, morpholinyl, benzoxazolyl, benzimidazolyl-, benzothiazolyl, carbazyl, azepines base and triazinyl; Silyl, the quantity of its carbon atom is 3-40 preferably, more preferably 3-30,3-24 most preferably is such as trimethyl silyl and triphenyl silyl; Siloxy-, the quantity of its carbon atom is 3-30 preferably, and more preferably 6-30 is such as triphenyl siloxy-, t-butyldimethylsilyloxy base; Deng.These substituting groups can also be substituted.R ¹¹Alkyl or aryl preferably.

In general formula (1), n ¹¹Represent 0 or bigger integer, preferred 0-5, more preferably 0-2, most preferably 1.

From the angle of the vapor deposition of preparation during the luminaire, the phenyl ring quantity in the compound (1) preferably 15 or still less.Equally, when compound (1) comprises the group that condenses with 4 or more a plurality of rings, during as pyrenyl, triphenylenyl etc., the quantity that condenses group with 4 or more a plurality of rings preferably 2 or still less.

Compound (1), preferably by following general formula (5) or (6) expression, is most preferably represented by general formula (5) more preferably by general formula (2) expression more preferably by following general formula (2), (3) or (4) expression.The compound of general formula (4) representative is preferably represented by following general formula (6).

In general formula (2), Ar ²¹, Ar ²², Ar ²³, Ar ²⁴And Ar ²⁵Represent aryl or heteroaryl separately, preferably represent aryl.Ar ²¹, Ar ²², Ar ²³, Ar ²⁴And Ar ²⁵Can have a substituting group separately.Substituent example can with above-mentioned R ¹¹Those are identical.Ar ²¹, Ar ²², Ar ²³, Ar ²⁴And Ar ²⁵In at least one is fused-aryl, condenses or the heteroaryl or of uncondensed comprises fused-aryl or condenses or the group of the heteroaryl of uncondensed.

Ar ²¹, Ar ²², Ar ²³And Ar ²⁴Preferably phenyl, naphthyl, anthryl, phenanthryl or fluoranthene base are more preferably phenyl, naphthyl, anthryl or phenanthryl separately, and preferably phenyl, naphthyl or phenanthryl most preferably are phenyl again.Ar ²⁵Preferably phenyl, naphthyl, phenanthryl, anthryl, pyrenyl, perylene base or fluoranthene base are more preferably phenanthryl, anthryl or pyrenyl, most preferably are pyrenyls.Ar ²¹, Ar ²², Ar ²³, Ar ²⁴And Ar ²⁵Do not link to each other each other and form ring.

In general formula (2), R ²¹Represent a hydrogen atom or a substituting group.Substituent example can with above-mentioned R ¹¹Those are identical.R ²¹Preferably hydrogen atom, alkyl or aryl are more preferably hydrogen atom, phenyl or pyrenyl, most preferably are pyrenyls.

In general formula (3), Ar ³¹, Ar ³², Ar ³³, Ar ³⁴, Ar ³⁵, Ar ³⁶, Ar ³⁷And Ar ³⁸Represent aryl or heteroaryl separately.Ar ³¹, Ar ³², Ar ³³, Ar ³⁴, Ar ³⁵, Ar ³⁶, Ar ³⁷And Ar ³⁸Separately a substituting group can be arranged, the example can with above-mentioned R ¹¹Those are identical.Ar ³¹, Ar ³², Ar ³³, Ar ³⁴, Ar ³⁵, Ar ³⁶, Ar ³⁷And Ar ³⁸Do not link to each other each other and form ring.Ar ³¹, Ar ³², Ar ³³, Ar ³⁴, Ar ³⁵, Ar ³⁶, Ar ³⁷And Ar ³⁸Aryl preferably is more preferably phenyl, naphthyl, anthryl, pyrenyl or phenanthryl separately, most preferably is phenyl.

In general formula (4), Ar ⁴¹, Ar ⁴², Ar ⁴³, Ar ⁴⁴, Ar ⁴⁵, Ar ⁴⁶, Ar ⁴⁷, Ar ⁴⁸, Ar ⁴⁹And Ar ⁵⁰Represent aryl or heteroaryl separately.Ar ⁴¹, Ar ⁴², Ar ⁴³, Ar ⁴⁴, Ar ⁴⁵, Ar ⁴⁶, Ar ⁴⁷, Ar ⁴⁸, Ar ⁴⁹And Ar ⁵⁰Separately a substituting group can be arranged, the example can with above-mentioned R ¹¹Those are identical.Ar ⁴¹, Ar ⁴², Ar ⁴³, Ar ⁴⁴Ar ⁴⁵, Ar ⁴⁶Ar ⁴⁷Ar ⁴⁸Ar ⁴⁹And Ar ⁵⁰Do not link to each other each other and form ring.Ar ⁴¹, Ar ⁴², Ar ⁴³, Ar ⁴⁴, Ar ⁴⁵, Ar ⁴⁶, Ar ⁴⁷, Ar ⁴⁸, Ar ⁴⁹And Ar ⁵⁰Aryl preferably is more preferably phenyl, naphthyl, anthryl, pyrenyl or phenanthryl separately, most preferably is phenyl.

In general formula (5), Ar ⁵¹, Ar ⁵², Ar ⁵³And Ar ⁵⁴Represent aryl separately, preferably represent phenyl, naphthyl, anthryl, phenanthryl or fluoranthene base, more preferably represent phenyl, naphthyl, anthryl or phenanthryl, preferably represent phenyl, naphthyl or phenanthryl again, most preferably represent phenyl.Ar ⁵¹, Ar ⁵², Ar ⁵³And Ar ⁵⁴Separately a substituting group can be arranged, the example can with above-mentioned R ¹¹Those are identical.

In general formula (5), R ⁵¹Represent a hydrogen atom or a substituting group.Substituent example can with above-mentioned R ¹¹Those are identical.R ⁵¹Preferably hydrogen atom, alkyl or aryl, more preferably hydrogen atom, phenyl or pyrenyl, most preferably pyrenyl.

In general formula (5), R ⁵²Represent a substituting group, the example can with above-mentioned R ¹¹Those are identical.R ⁵²Alkyl or aryl preferably.n ⁵¹Represent R ⁵²Quantity, it is the integer of 0-9, preferably 0-2 is more preferably 0.The quantity of the pyrenyl in the compound of general formula (5) representative preferably 2 or still less.

In general formula (6), aspect definition and preferred embodiment, Ar ⁶¹And Ar ⁶⁸With top Ar ²¹Identical; Ar ⁶²And Ar ⁶⁷With top Ar ²²Identical; Ar ⁶³And Ar ⁶⁶With top Ar ²³Identical; And Ar ⁶⁴And Ar ⁶⁵With top Ar ²⁴Identical.Ar ⁶¹, Ar ⁶², Ar ⁶³, Ar ⁶⁴, Ar ⁶⁵, Ar ⁶⁶, Ar ⁶⁷And Ar ⁶⁸Separately a substituting group can be arranged, the example can with above-mentioned R ¹¹Those are identical.n ⁶¹And n ⁶²Represent the integer of 0-5 separately, preferred 0-3, more preferably 0 or 1.

In general formula (6), R ⁶¹And R ⁶²Its definition and preferred embodiment aspect and above R ²¹Identical.R ⁶³, R ⁶⁴And R ⁶⁵Its definition and preferred embodiment aspect and above R ⁵²Identical.n ⁶³And n ⁶⁴Represent the integer of 0-4 separately, preferred 0 or 1, more preferably 0.n ⁶⁵Represent the integer of 0-8, preferred 0-2, more preferably 0.

Compound (1) is low-molecular weight compound preferably, and it can be oligopolymer or polymkeric substance.At compound (1) is under the situation of polymkeric substance or oligopolymer, is its weight-average molecular weight preferably 1 of standard test with the polystyrene, 000-5,000,000, more preferably 2,000-1,000,000, most preferably 3,000-100,000.Described polymkeric substance can contain the part of formula (1) representative in its main chain or side chain.Described polymkeric substance can be homopolymer or multipolymer.

Compound (1) preferably has the maximum emission wavelength λ of 370-500nm in the fluorescence spectrum of its individual layer or powder _Maxλ _MaxBe more preferably 390-480nm, 400-460nm preferably most preferably is 400-440nm again.

The compound of general formula (1) representative, the compound that is used for the compound of electronic conductive layer and is used for hole-conductive layer have preferred 100 ℃ or higher second-order transition temperature Tg separately, more preferably 120 ℃ or higher, preferred again 140 ℃ or higher, preferred especially 160 ℃ or higher.

Luminaire of the present invention also preferably contains at least a fluorescent chemicals at its luminescent layer.Described herein as the luminescent layer material compound and derivative in the preferable range of these fluorescent chemicalses.

The specific examples of compound (1) is described below without limitation.

The compound of general formula (1)-(6) representative can purifying.Purification process has no particular limits, but can be recrystallize method, column chromatography, sublimation purification method etc.

The sublimation purification method is known, and can be that for example " Lecture One onExperimental Chemistry; Basic Operations[I] " published by Maruzen company limited, method described in the 425-430 page or leaf, the method described in JP 5-269371 A, JP 6-263438 A, JP7-24205 A, JP 7-204402 A, JP 11-171801 A, JP 2000-93701 A, JP2000-48955 A, JP 62-22960 B, JP 2583306 B, JP 2706936 B etc.Sublimation purification can be carried out in vacuum or inert gas flow such as nitrogen, argon gas etc.The vacuum pump that carries out sublimation purification under vacuum has no particular limits, but can be rotor pump, turbomolecular pump, diffusion pump etc.

Compound (1) can be synthetic by the currently known methods described in the following document: Tetrahedron, the 15349th page of the 1997,53, the 45th phase; J.Am.Chem.Soc., the 1996,118,741st page; J.Org.Chem.Soc., the 1986,51,979th page; Angew.Chem.Int.Ed.Engl., the 1997,36,631st page; Indian J.Chem.Sect.B, the 2000,39,173rd page; Org.Synth.Coll. the 5th phase, 1973, the 604 pages; Chem.Ber., the 1960,93,1769th page etc.

Although luminaire of the present invention has no particular limits at aspects such as its system, driving method and purposes, described luminaire preferably has use compound (1) as luminescent material or as the structure of material of main part, electronics injecting material, electrically conductive material, hole-injecting material and/or hole-conductive material.Known typical luminaire is organic electroluminescent (EL) equipment.

Luminaire of the present invention comprises a luminescent layer and a plurality of organic layers that comprise a luminescent layer between pair of electrodes (anode and negative electrode).Described luminescent layer or at least one organic layer comprise compound (1).When compound of the present invention was used as luminescent material, the amount of the compound (1) in the layer of inclusion compound (1) is 0.1-100 quality % preferably, is more preferably 0.5-100 quality %.When compound (1) was used as material of main part, the amount of compound (1) is 10-99.9 quality % preferably, is more preferably 20-99.5 quality %.

The formation of the layer of inclusion compound (1) has no particular limits, and this layer can pass through resistive heating vapor deposition process, electronic beam method, sputtering method, packing of molecules method, coating method, ink-jet printing process, impact system, transfer method, electrophotographic method etc.From the performance of luminaire and the angle of production cost, wherein preferred resistive heating vapor deposition process, coating method and impact system.

Except luminescent layer, luminaire of the present invention can comprise functional layer, as hole injection layer, hole-conductive layer, electron injecting layer, electronic conductive layer, protective layer etc.Described functional layer can have other function.Compound (1) can be contained in any these layers.Describe each element of luminaire of the present invention below in detail.

(A) anode

Anode plays a part to provide the hole to hole injection layer, hole-conductive layer, luminescent layer etc.Anode is made by pure metal, alloy, metal oxide, conductive compound and their mixture etc. usually, is preferably made by the material with 4eV or higher work function.The example of anode material comprises metal, for example gold and silver, chromium, nickel and their alloy; Conducting metal oxide, for example stannic oxide, zinc oxide, Indium sesquioxide and indium tin oxide target (ITO); The mixture of these metals and conducting metal oxide and laminate; Conduction mineral compound, for example cupric iodide and cupric sulfide; Conductive organic compound, for example polyaniline, Polythiophene and polypyrrole; The laminate of conductive organic compound and ITO; Or the like.From the angle of productivity, electroconductibility, transparency etc., anode is preferably by conducting metal oxide, and particularly ITO makes.

Can select anodic formation method according to used material.For example, the anode of making by ITO can be by electronic beam method, sputtering method, resistive heating vapor deposition process, chemical reaction method such as sol-gel method, use the coating method of the dispersion liquid that contains indium tin oxide target etc.Anode can stand carrying out washing treatment etc., to reduce the luminous efficiency of driving voltage or increase luminaire.For example, under the situation that is ito anode, UV-ozonize and Cement Composite Treated by Plasma are effective.Anode preferably has hundreds of Q/ square or littler sheet resistance.Although can roughly determine anodic thickness according to used material, preferred in general 10nm-5 μ m, more preferably 50nm-1 μ m, most preferably 100-500nm.

Anode is usually located on the substrate of being made by soda-lime glass, non-alkali glass, transparent resin etc.Glass substrate is preferably made to reduce the ion wash-out by non-alkali glass.Under the situation of using soda-lime glass, preferably form the barrier coatings of silicon-dioxide etc. in advance thereon.The thickness of substrate has no particular limits, as long as it has enough intensity.Under the situation that is glass substrate, the thickness of substrate is 0.2mm or bigger, preferred 0.7mm or bigger normally.

(B) negative electrode

Negative electrode plays a part to supplies electrons such as electron injecting layer, electronic conductive layer, luminescent layers.Bonding etc. according to ionization potential, stability, the layer (as luminescent layer) adjacent, the material of negative electrode with negative electrode can be selected from pure metal, alloy, metal halide, metal oxide, conductive compound, and composition thereof etc.The example of cathode material comprises basic metal such as Li, Na and K and fluorochemical and oxide compound; Alkaline-earth metal such as Mg and Ca and fluorochemical thereof and oxide compound; Gold; Silver; Plumbous; Aluminium; The alloys and mixts of sodium and potassium; The alloys and mixts of lithium and aluminium; Magnesium and silver-colored alloys and mixts; Rare earth metal such as indium and ytterbium; And their mixture; Or the like.Negative electrode is that 4eV or littler material are made by work function preferably, and more preferably by the alloy or the mixture of aluminium, lithium and aluminium, or the alloys and mixts of magnesium and silver is made.

Negative electrode can have single layer structure or multilayered structure.Preferred multilayered structure is aluminium/lithium fluoride, aluminium/Lithium Oxide 98min etc.Negative electrode can pass through formation such as electronic beam method, sputtering method, resistive heating vapor deposition process, coating method.Can deposit multiple material simultaneously by vapor deposition process.Alloy cathode can be by depositing multiple metal or forming by their alloy of deposition simultaneously.Negative electrode preferably has hundreds of Q/ square or littler sheet resistance.Although the thickness of negative electrode can roughly be determined according to material therefor, usually preferred 10nm-5 μ m, more preferably 50nm-1 μ m, most preferably 100nm-1 μ m.

(C) hole injection layer and hole-conductive layer

The material that is used for hole injection layer and hole-conductive layer has no particular limits, as long as they have any following function: will be injected into by the hole that anode provides in the luminescent layer; Hole-conductive is arrived luminescent layer; The electronics that provides by negative electrode with blocking-up.The example of described material comprises carbazole, triazole oxazole oxadiazole, imidazoles, poly-aryl paraffinic, pyrazoline, pyrazolone, phenylenediamine, the aryl amine, the amino phenyl styryl ketone that replaces, the styryl anthracene, Fluorenone, hydrazone, toluylene, silazane, aromatic tertiary amine compound, the styryl amine compound, fragrance two methylidyne compounds, porphyrin compound, polysilane compound, poly-(N-vinylcarbazole), aniline, conductive polymers and oligopolymer such as oligothiophene and Polythiophene, organic silane compound, compound (1), its derivative, carbon etc.

Hole injection layer and hole-conductive layer can be individual layer of being made by one or more materials or the multilayer that is made from the same material or a different material separately.Hole injection layer and hole-conductive layer can be by vacuum deposition methods, LB method, use formation such as containing the solution of flooring or the coating method of dispersion liquid (as spin-coating method, teeming practice and dip coating), ink-jet printing process, impact system, transfer method, electrophotographic method.The solution and the dispersion liquid that are used for coating method can contain a resin.The example of these resins comprises poly-(vinylchlorid), polycarbonate-based, polystyrene, poly-(methyl methacrylate), poly-(butyl methacrylate), polyester, polysulfones, poly-(phenylate), polyhutadiene, poly-(N-vinylcarbazole), the hydrocarbon resin class, the ketone resin class, phenoxy lipid, polyamide-based, ethyl cellulose, poly-(vinyl-acetic ester), the ABS resin class, polyurethanes, the melamine resin class, the unsaturated polyester resin class, the Synolac class, epoxy resin, polyorganosiloxane resin class etc.Although hole injection layer and hole-conductive layer thickness are separately had no particular limits, preferred in general 1nm-5 μ m, more preferably 5nm-1 μ m, particularly 10-500nm.

(D) luminescent layer

In luminescent layer, when when described luminaire applies electric field, will be by anode, hole injection layer or hole-conductive layer injected holes with compound by negative electrode, electron injecting layer or electronic conductive layer injected electrons, thus luminous.Luminescent material and fluorescent chemicals to described luminescent layer have no particular limits, as long as they have following function: the hole that is provided by anode etc. is provided; The electronics that reception is provided by negative electrode etc.; Conduct charges; And when luminaire applies electric field with hole and electron recombination with luminous.The example of luminescent material comprises benzoxazole; Benzoglyoxaline; Benzothiazole; Styryl benzene; Polyphenylene; Diphenyl diethylene; Tetraphenylbutadiene; Naphthalimido; Tonka bean camphor; Perynone; Oxadiazole; Aldazine; Pyralidine; Cyclopentadiene; Two (styryl) anthracene; Quinacridone; Pyrrolopyridine; Thiadiazoles and pyridine; Cyclopentadiene; Styryl amine; Fragrance two methylidyne compounds; Pyrromethene; Fused aromatic compounds such as anthracene, pyrene, fluoranthene, perylene; Metal complex such as 8-quinolinol derivant metal complex compound; High-molecular weight luminescent material (as Polythiophene, polyphenylene and polyphenylene vinylene); Organic silane compound; Compound (1); Their derivative; Or the like.

Luminescent layer can be made by one or more materials.Luminaire of the present invention can comprise one or more luminescent layers.Comprise at luminaire under the situation of a plurality of luminescent layers that each luminescent layer can be made by one or more materials, and can send the light of different colours, so that white light to be provided.Single luminescent layer can provide white light.

Luminescent layer can pass through the resistive heating vapor deposition process; Electronic beam method; Sputtering method; The packing of molecules method; Coating method (as spin-coating method, teeming practice and dip coating); Ink-jet printing process; Impact system; The LB method; Transfer method; Electrophotographic method; Or the like form wherein preferred resistive heating vapor deposition process and coating method.Although the thickness of luminescent layer has no particular limits, preferred in general 1nm-5 μ m, more preferably 5nm-1 μ m, particularly 10-500nm.

(E) electron injecting layer and electronic conductive layer

Have no particular limits for the material that is used for electron injecting layer and electronic conductive layer, as long as they have following arbitrarily function; To be injected into by the electronics that negative electrode provides in the luminescent layer; Electronic conduction is arrived luminescent layer; The hole that provides by anode with blocking-up.The example of these materials comprises triazole; Oxazole; Oxadiazole; Imidazoles; Fluorenone; The anthraquinone bismethane; Anthrone; The phenylbenzene quinone; The titanium dioxide thiapyran; Carbodiimide; Fluorenylidene methane; The diphenylethyllene pyrazine; Tetracarboxylic anhydride with aromatic nucleus (for example naphthalene nucleus is with perylene ring etc.); Phthalocyanine; Metal complex such as 8-quinolinol derivant metal complex compound, metal phthalocyanine complex and contain benzoxazole or benzothiazole as the metal complex of part; Metal (as aluminium, zinc, gallium, beryllium, magnesium); Organic silane compound; Compound (1); Their derivative; Or the like.

Electron injecting layer and electronic conductive layer can have single layer structure of being made by one or more materials or the multilayered structure that is made from the same material or a different material separately.Electron injecting layer and electronic conductive layer can pass through vacuum deposition method; The LB method; Use contains the solution of flooring or the coating method of dispersion liquid (as dip coating, teeming practice and dip coating); Ink-jet printing process; Impact system; Transfer method; Electrophotographic method; Or the like.The solution and the dispersion liquid that are used for coating method can contain a resin.The example of these resins can be used for the identical of hole injection layer and hole-conductive layer.Although electron injecting layer and electronic conductive layer thickness are separately had no particular limits, its preferred 1nm-5 μ m, more preferably 5nm-1 μ m, particularly 10-500nm in general.

(F) protective layer

Protective layer plays a part to cover luminaire to prevent infiltration damage equipments such as water branch, oxygen.The example that is used for the material of protective layer comprises metal (as In, Sn, Pb, Au, Cu, Ag, Al, Ti and Ni); Metal oxide is (as MgO, SiO, SiO ₂, Al ₂O ₃, GeO, NiO, CaO, BaO, Fe ₂O ₃, Y ₂O ₃And TiO ₂); Metal fluoride is (as MgF ₂, LiF, AlF ₃And CaF ₂); Nitride is (as SiN _xAnd SiO _xN _y); Polyethylene; Polypropylene; Polymethylmethacrylate; Poly-imines class; Polyureas; Tetrafluoroethylene; Polychlorotrifluoroethylene; Poly-dichloro difluoroethylene; The multipolymer of chlorotrifluoroethylene and dichloro difluoroethylene; The multipolymer of tetrafluoroethylene and at least a comonomer; Fluorinated copolymer with main chain of band structure; Water-intake rate is 1% or bigger water-absorbing material; Water-intake rate is 0.1% or littler water-proof material; Or the like.

The method that forms protective layer has no particular limits.Protective layer can pass through vacuum deposition method, sputtering method, reactive sputtering method, molecular beam epitaxy (MBE) method, ion beam method, ion plating method, high frequency excitation ion plating method, Plasma Polymerization, plasma CVD method, laser CVD method, hot CVD method, gas source CVD method, coating method, impact system, transfer method etc.

Specifically describe the present invention below with reference to embodiment, but do not plan to limit the scope of the invention.

Synthetic embodiment 1

Synthesizing of compound (1-1)

With between 10ml-dimethylbenzene joins in 0.5g 1-ethynyl pyrene and the 0.85g tetraphenylcyclopentadienone and stirred 3 hours under refluxing.The gained reaction product solution is cooled to room temperature, and to wherein adding 50ml methyl alcohol with precipitated solid.Filtration with solids constituent from, and by silica gel column chromatography purifying (hexane/chloroform=5/1), obtain the 1.1g white solid.Mass spectroscopy confirms that this white solid is compound (1-1).This result hints that compound (1-1) obtains by following reaction.

Synthetic embodiment 2

Synthesizing of compound (1-47)

The 50ml phenyl ether is joined in following compd A of 1g and the 1.35g tetraphenylcyclopentadienone and under refluxing, stirred 30 hours.The gained reaction product solution is cooled to room temperature, and to wherein adding 100ml methyl alcohol with precipitated solid.Filtration with solids constituent from, and by silica gel column chromatography purifying (chloroform), obtain the 1.3g white solid.Mass spectroscopy confirms that this white solid is compound (1-47).This result hints that compound (1-47) obtains by following reaction.

Synthetic embodiment 3

Synthesizing of compound (1-15)

The 50ml phenyl ether is joined in following compd B of 1g and the 3g tetraphenylcyclopentadienone and under refluxing, stirred 10 hours.The gained reaction product solution is cooled to room temperature, and to wherein adding 100ml methyl alcohol with precipitated solid.Filtration with solids constituent from, and by silica gel column chromatography purifying (chloroform), obtain the 2.0g white solid.Mass spectroscopy confirms that this white solid is compound (1-15).This result hints that compound (1-15) obtains by following reaction.

Synthetic embodiment 4

Synthesizing of compound (1-2)

The 10ml phenyl ether is joined in following Compound C of 0.5g and the 0.85g tetraphenylcyclopentadienone and under refluxing, the gained reaction mixture was stirred 3 hours.The gained reaction product solution is cooled to room temperature, and to wherein adding 50ml methyl alcohol with precipitated solid.Filtration with solids constituent from, and by silica gel column chromatography purifying (hexane/chloroform=5/1), obtain the 1.0g white solid.Mass spectroscopy confirms that this white solid is compound (1-2).This result hints that compound (1-2) obtains by following reaction.

Synthetic embodiment 5

Synthesizing of compound (1-14)

The 50ml phenyl ether is joined in following Compound D of 0.5g and the 3g tetraphenylcyclopentadienone and under refluxing, stirred 10 hours.The gained reaction product solution is cooled to room temperature, and to wherein adding 100ml methyl alcohol with precipitated solid.Filtration with solids constituent from, and by silica gel column chromatography purifying (chloroform), obtain the 0.9g faint yellow solid.Mass spectroscopy confirms that this faint yellow solid is compound (1-14).This result hints that compound (1-14) obtains by following reaction.

Compound b-the v that is used for following examples and comparative example is described below.

The compound b compound c

Compound d Verbindung compound f

Compound g compound h

Compound i compound j

Compound k compound m compound n

Compound q compound r

Compound t

Compound u compound v

The comparative example 1

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With top toluylene based compound (compound b) thereon, then with the thickness vapor deposition of 40nm thereon with top azole compounds (compound c) with the thickness vapor deposition of 20nm.After the mask deposition of the required light-emitting area that will delineate 4mm * 5mm is on the gained organic film, with magnesium and silver (magnesium/silver-colored mass ratio is 10: 1) on the organic film of thickness codeposition in depositing device with 50nm, and thereon again vapor deposition thickness be the silver of 50nm, make a luminaire.

Applying volts DS by " the Source-Measure Unit 2400 " that can obtain from Toyo company to comparative example 1 luminaire makes it luminous, by can measuring luminous brightness from " the Luminance Meter BM-8 " that Topcon company obtains, and " Spectral Analyzer PMA-11 " mensuration emission wavelength by obtaining from Hamamatsu Photonics K.K..Found that comparative example 1 luminaire is with high-high brightness 1,130cd/m ²Send the bluish-green coloured light of colourity for (0.15,0.20).After this luminaire placed one day in nitrogen environment, the laminar surface of observing this luminaire had shade.

Embodiment 1

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1) thereon, then with the thickness vapor deposition of 40nm thereon with azole compounds (compound c) with the thickness vapor deposition of 20nm.After the mask deposition of the required light-emitting area that will delineate 4mm * 5mm is on the gained organic film, with magnesium and silver (magnesium/silver-colored mass ratio is 10: 1) on the organic film of thickness codeposition in depositing device with 50nm, and thereon again vapor deposition thickness be the silver of 50nm, make a luminaire.For the light that sends from this luminaire, measure brightness and emission wavelength in the mode identical with comparative example 1.Found that this luminaire is with high-high brightness 4,370cd/m ²Send the blue light of colourity for (0.15,0.10).The external quantum efficiency φ of this luminaire _EL=1.4% (calculated value).After this luminaire placed one day in nitrogen environment, the laminar surface of observing this luminaire was transparent.

Embodiment 2

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-17) thereon, then with the thickness vapor deposition of 40nm thereon with azole compounds (compound c) with the thickness vapor deposition of 20nm.After the mask deposition of the required light-emitting area that will delineate 4mm * 5mm is on the gained organic film, with magnesium and silver (magnesium/silver-colored mass ratio is 10: 1) on the organic film of thickness codeposition in depositing device with 50nm, and thereon again vapor deposition thickness be the silver of 50nm, make a luminaire.For the light that sends from this luminaire, measure brightness and emission wavelength in the mode identical with comparative example 1.Found that this luminaire is with high-high brightness 2,920cd/m ²Send the blue light of colourity for (0.15,0.14).The external quantum efficiency φ of this luminaire _EL=1.3% (calculated value).After this luminaire placed one day in nitrogen environment, the laminar surface of observing this luminaire was transparent.

Embodiment 3

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-24) thereon, then with the thickness vapor deposition of 40nm thereon with azole compounds (compound c) with the thickness vapor deposition of 20nm.After the mask deposition of the required light-emitting area that will delineate 4mm * 5mm is on the gained organic film, with magnesium and silver (magnesium/silver-colored mass ratio is 10: 1) on the organic film of thickness codeposition in depositing device with 50nm, and thereon again vapor deposition thickness be the silver of 50nm, make a luminaire.For the light that sends from this luminaire, measure brightness and emission wavelength in the mode identical with comparative example 1.Found that this luminaire is with high-high brightness 2,000cd/m ²Send the blue light of colourity for (0.15,0.18).The external quantum efficiency φ of this luminaire _EL=1.3% (calculated value).After this luminaire placed one day in nitrogen environment, the laminar surface of observing this luminaire was transparent.

Embodiment 4

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1) and 7,4-(dicyano methylene radical)-2-methyl-6-(4-dimethylamino styryl)-4H-pyrans (DCM) (wherein the mass ratio of compound (1-1) and DCM is 1000: 5) with the thickness codeposition of 20nm thereon, then with the thickness vapor deposition of 40nm thereon with azole compounds (compound c).After the mask deposition of the required light-emitting area that will delineate 4mm * 5mm is on the gained organic film, with magnesium and silver (magnesium/silver-colored mass ratio is 10: 1) on the organic film of thickness codeposition in depositing device with 50nm, and thereon again vapor deposition thickness be the silver of 50nm, make a luminaire.For the light that sends from this luminaire, measure brightness and emission wavelength in the mode identical with comparative example 1.Found that this luminaire is with high-high brightness 4,300cd/m ²Send the white light of colourity for (0.30,0.32).The external quantum efficiency φ of this luminaire _EL=2.2% (calculated value).After this luminaire placed one day in nitrogen environment, the laminar surface of observing this luminaire was transparent.

Embodiment 5

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With three (oxine acidic group) aluminium (Alq) and DCM (wherein the mass ratio of Alq and DCM is 100: 1) thereon with the thickness codeposition of 5nm, again with the thickness vapor deposition of 15nm thereon, then with the thickness vapor deposition of 40nm thereon with azole compounds (compound c) with compound (1-1).After the mask deposition of the required light-emitting area that will delineate 4mm * 5mm is on the gained organic film, with magnesium and silver (magnesium/silver-colored mass ratio is 10: 1) on the organic film of thickness codeposition in depositing device with 50nm, and thereon again vapor deposition thickness be the silver of 50nm, make a luminaire.For the light that sends from this luminaire, measure brightness and emission wavelength in the mode identical with comparative example 1.Found that this luminaire is with high-high brightness 4,400cd/m ²Send the white light of colourity for (0.31,0.33).The external quantum efficiency φ of this luminaire _EL=2.3% (calculated value).After this luminaire placed one day in nitrogen environment, the laminar surface of observing this luminaire was transparent.

Embodiment 6

With 40mg poly-(N-vinylcarbazole), 12mg 2-(4-tert-butyl-phenyl)-5-(4-xenyl)-1,3,4-oxadiazole and 1mg compound (1-1) are dissolved in the 2.5ml ethylene dichloride.1, under the 500rpm and the condition in 20 seconds gained solution is spun on the clean ITO substrate, forming thickness is the organic layer of 110nm.After the mask deposition of the required light-emitting area that will delineate 4mm * 5mm is on the gained organic film, with magnesium and silver (magnesium/silver-colored mass ratio is 10: 1) on the organic film of thickness codeposition in depositing device with 50nm, and thereon again vapor deposition thickness be the silver of 50nm, make a luminaire.For the light that sends from this luminaire, measure brightness and emission wavelength in the mode identical with comparative example 1.Found that this luminaire is with high-high brightness 1,900cd/m ²Send the blue light of colourity for (0.15,0.10).

Embodiment 7

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-15) thereon, then with the thickness vapor deposition of 40nm thereon with azole compounds (compound c) with the thickness vapor deposition of 20nm.After the mask deposition of the required light-emitting area that will delineate 4mm * 5mm is on the gained organic film, with magnesium and silver (magnesium/silver-colored mass ratio is 10: 1) on the organic film of thickness codeposition in depositing device with 50nm, and thereon again vapor deposition thickness be the silver of 50nm, make a luminaire.For the light that sends from this luminaire, measure brightness and emission wavelength in the mode identical with comparative example 1.Found that this luminaire is with high-high brightness 3,200cd/m ²Send the blue light of colourity for (0.16,0.08).The external quantum efficiency φ of this luminaire _EL=1.2% (calculated value).After this luminaire placed one day in nitrogen environment, the laminar surface of observing this luminaire was transparent.

Embodiment 8

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-2) thereon, then with the thickness vapor deposition of 40nm thereon with azole compounds (compound c) with the thickness vapor deposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.For the light that sends from this luminaire, measure brightness and emission wavelength in the mode identical with comparative example 1.Found that this luminaire is with high-high brightness 1,400cd/m ²Send the blue light of colourity for (0.16,0.08).The external quantum efficiency φ of this luminaire _EL=1.5% (calculated value).After this luminaire placed one day in nitrogen environment, the laminar surface of observing this luminaire was transparent.

Embodiment 9

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-47) thereon, then with the thickness vapor deposition of 40nm thereon with azole compounds (compound c) with the thickness vapor deposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.For the light that sends from this luminaire, measure brightness and emission wavelength in the mode identical with comparative example 1.Found that this luminaire is with high-high brightness 6,470cd/m ²Send the blue light of colourity for (0.17,0.17).The external quantum efficiency φ of this luminaire _EL=3.4% (calculated value).After this luminaire placed one day in nitrogen environment, the laminar surface of observing this luminaire was transparent.

Embodiment 10

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-14) thereon, then with the thickness vapor deposition of 40nm thereon with azole compounds (compound c) with the thickness vapor deposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.For the light that sends from this luminaire, measure brightness and emission wavelength in the mode identical with comparative example 1.Found that this luminaire is with high-high brightness 2,500cd/m ²Send the blue light of colourity for (0.16,0.17).The external quantum efficiency φ of this luminaire _EL=0.8% (calculated value).After this luminaire placed one day in nitrogen environment, the laminar surface of observing this luminaire was transparent.

Embodiment 11

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1) thereon, then with the thickness vapor deposition of 40nm thereon with compound d with the thickness vapor deposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Applying under the voltage condition of 8V, it is 1 that this luminaire sends brightness, 100cd/m ²Blue light.

Embodiment 12

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-47) thereon, then with the thickness vapor deposition of 40nm thereon with Verbindung with the thickness vapor deposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 9V, it is 1 that this luminaire sends brightness, 300cd/m ²Blue light.

Embodiment 13

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-47) thereon, then with the thickness vapor deposition of 40nm thereon with compound f with the thickness vapor deposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 9V, it is 1 that this luminaire sends brightness, 200cd/m ²Blue light.

Embodiment 14

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1) and compound g (wherein compound (1-1) is 100: 1 with the mass ratio of compound g) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 7V, it is 2 that this luminaire sends brightness, 500cd/m ²Orange-colored light.

Embodiment 15

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1) and compound h (wherein compound (1-1) is 100: 1 with the mass ratio of compound h) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 7V, it is 1 that this luminaire sends brightness, 800cd/m ²Red light.

Embodiment 16

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1) and compound i (wherein compound (1-1) is 100: 1 with the mass ratio of compound i) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 7V, it is 6 that this luminaire sends brightness, 300cd/m ²Green light.

Embodiment 17

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-2) and compound j (wherein compound (1-2) is 100: 1 with the mass ratio of compound j) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 7V, it is 4 that this luminaire sends brightness, 500cd/m ²Yellow-green light.

Embodiment 18

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-47) and compound k (wherein compound (1-47) is 100: 1 with the mass ratio of compound k) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 7V, it is 3 that this luminaire sends brightness, 900cd/m ²Sodium yellow.

Embodiment 19

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1) and compound m (wherein compound (1-1) is 10: 1 with the mass ratio of compound m) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 8V, it is 2 that this luminaire sends brightness, 800cd/m ²Blue light.

Embodiment 20

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-47) and compound m (wherein compound (1-47) is 10: 1 with the mass ratio of compound m) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 8V, it is 3 that this luminaire sends brightness, 400cd/m ²Bluish-green coloured light.

Embodiment 21

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1) and compound n (wherein compound (1-1) is 1: 1 with the mass ratio of compound n) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 8V, it is 1 that this luminaire sends brightness, 100cd/m ²Blue light.

Embodiment 22

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1) and compound o thereon, then with the thickness vapor deposition of 40nm thereon with compound c with thickness (wherein compound (1-1) is 10: 1 with the mass ratio of the compound o) codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 8V, this luminaire sends 1,800cd/m ²Blue light.

Embodiment 23

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1) and compound p (wherein compound (1-1) is 20: 1 with the mass ratio of compound p) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 8V, it is 3 that this luminaire sends brightness, 800cd/m ²Blue light.

Embodiment 24

With compound q with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness vapor deposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 8V, it is 2 that this luminaire sends brightness, 100cd/m ²Blue light.

Embodiment 25

With compound r with the thickness vapor deposition of 10nm to the clean ITO substrate that is placed in the depositing device.With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl are (α-NPD) with the thickness vapor deposition of 30nm thereon, again with compound (1-1) with the thickness vapor deposition of 20nm thereon.Then with the thickness vapor deposition of 40nm thereon with compound c.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 6V, it is 2 that this luminaire sends brightness, 200cd/m ²Blue light.

Embodiment 26

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1) and compound (1-2) (wherein compound (1-1) is 1: 1 with the mass ratio of compound (1-2)) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 8V, it is 2 that this luminaire sends brightness, 200cd/m ²Blue light.

Embodiment 27

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound d and compound k (wherein the mass ratio of compound d and compound k is 100: 1) thereon, then with the thickness codeposition of 20nm thereon with compound (1-1) and compound p (wherein compound (1-1) is 20: 1 with the mass ratio of compound p) with the thickness codeposition of 5nm.Again with the thickness vapor deposition of 20nm thereon with compound c.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 8V, it is 4 that this luminaire sends brightness, 100cd/m ²White light.

Embodiment 28

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-14) and compound p (wherein compound (1-14) is 20: 1 with the mass ratio of compound p) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 8V, it is 2 that this luminaire sends brightness, 900cd/m ²Blue light.

Embodiment 29

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-14) and compound m (wherein compound (1-14) is 1: 1 with the mass ratio of compound m) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 8V, it is 3 that this luminaire sends brightness, 700cd/m ²Blue light.

Embodiment 30

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1), compound p and compound g (wherein the mass ratio of compound (1-1)/compound p/ compound g is 100: 5: O.2) thereon with the thickness codeposition of 20nm, then with the thickness vapor deposition of 40nm thereon with compound c.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 8 V, it is 1 that this luminaire sends brightness, 800cd/m ²White light.

Embodiment 31

1, under the condition in 000rpm and 30 seconds, with clean ITO substrate " Baytron P " (PEDOT-PSS solution, promptly be mixed with poly-(ethylidene dioxy base thiophene) solution of polystyrolsulfon acid, it can obtain from BAYER AG) spin coating, and 150 ℃ of following vacuum-dryings 1.5 hours, forming thickness was the organic layer of 70nm.1, with the 10mg polymethylmethacrylate in the thus obtained organic layer usefulness 4ml ethylene dichloride and 20 seconds of mixture spin coating of 30mg compound (1-1), forming total thickness is the organic layer of 120nm under the 500rpm.With compound c thereon with the thickness vapor deposition of 50nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 10V, it is 800cd/m that this luminaire sends brightness ²Blue light.

Embodiment 32

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1) thereon, then with the thickness vapor deposition of 40nm thereon with compound d with the thickness vapor deposition of 20nm.With LiF with the thickness vapor deposition of 3nm on the gained organic film, with the thickness vapor deposition aluminium of 100nm, make a luminaire then.Apply the voltage of 8V, it is 1 that this luminaire sends brightness, 300cd/m ²Blue light.

Embodiment 33

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-2) and compound s (wherein compound (1-2) is 100: 1 with the mass ratio of compound s) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 7V, it is 2 that this luminaire sends brightness, 500cd/m ²Green glow.

Embodiment 34

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-2) and compound t (wherein compound (1-2) is 1: 1 with the mass ratio of compound t) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 7V, it is 1 that this luminaire sends brightness, 500cd/m ²Blue light.

Embodiment 35

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-47) and compound u (wherein compound (1-47) is 100: 1 with the mass ratio of compound u) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 7 V, it is 2 that this luminaire sends brightness, 700cd/m ²Green light.

Embodiment 36

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-47) and compound v (wherein compound (1-47) is 100: 1 with the mass ratio of compound v) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 8V, it is 2 that this luminaire sends brightness, 200cd/m ²Orange-red light.

Embodiment 37

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-61) and compound p (wherein compound (1-61) is 100: 2 with the mass ratio of compound p) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 7V, it is 1 that this luminaire sends brightness, 000cd/m ²Blue light.

Embodiment 38

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-65) and compound s (wherein compound (1-65) is 100: 2 with the mass ratio of compound w) thereon, then with the thickness vapor deposition of 40nm thereon with compound c with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.Apply the voltage of 7V, it is 1 that this luminaire sends brightness, 100cd/m ²Blue light.

Embodiment 39

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-2) and compound p (wherein compound (1-2) is 95: 5 with the mass ratio of compound p) thereon, then with the thickness vapor deposition of 40nm thereon with azole compounds (compound c) with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.For the light that sends from this luminaire, measure brightness and emission wavelength in the mode identical with comparative example 1.Found that this luminaire is with high-high brightness 17,000cd/m ²Send the blue light of colourity for (0.16,0.18).The external quantum efficiency φ of this luminaire _EL=4% (calculated value).After this luminaire placed one day in nitrogen environment, the laminar surface of observing this luminaire was transparent.

Embodiment 40

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-47) and compound p (wherein compound (1-47) is 95: 5 with the mass ratio of compound p) thereon, then with the thickness vapor deposition of 40nm thereon with azole compounds (compound c) with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.For the light that sends from this luminaire, measure brightness and emission wavelength in the mode identical with comparative example 1.Found that this luminaire is with high-high brightness 10,000cd/m ²Send the blue light of colourity for (0.16,0.20).The external quantum efficiency φ of this luminaire _EL=3.5% (calculated value).After this luminaire placed one day in nitrogen environment, the laminar surface of observing this luminaire was transparent.

Embodiment 41

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-47) and compound p (wherein compound (1-2) is 99: 1 with the mass ratio of compound p) thereon, then with the thickness vapor deposition of 40nm thereon with azole compounds (compound c) with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.For the light that sends from this luminaire, measure brightness and emission wavelength in the mode identical with comparative example 1.Found that this luminaire is with high-high brightness 12,000cd/m ²Send the blue light of colourity for (0.16,0.18).The external quantum efficiency φ of this luminaire _EL=3.5% (calculated value).After this luminaire placed one day in nitrogen environment, the laminar surface of observing this luminaire was transparent.

Embodiment 42

With N, N '-phenylbenzene-N, N '-two (Alpha-Naphthyl) p-diaminodiphenyl (α-NPD) with the thickness vapor deposition of 40nm to the clean ITO substrate that is placed in the depositing device.With compound (1-1) and compound p (wherein compound (1-1) is 95: 5 with the mass ratio of compound p) thereon, then with the thickness vapor deposition of 40nm thereon with azole compounds (compound c) with the thickness codeposition of 20nm.Mode vapor deposition one negative electrode on the gained organic film with identical with comparative example 1 makes a luminaire.For the light that sends from this luminaire, measure brightness and emission wavelength in the mode identical with comparative example 1.Found that this luminaire is with high-high brightness 13,000cd/m ²Send the blue light of colourity for (0.15,0.22).The external quantum efficiency φ of this luminaire _EL=3.3% (calculated value).After this luminaire placed one day in nitrogen environment, the laminar surface of observing this luminaire was transparent.

Industrial applicibility

As what describe in detail above, luminaire of the present invention present excellent luminous efficiency, Luminescent properties, durability, heat resistance and the little amorphism of crystallization possibility. Have these spies The luminaire of the present invention of property can be used as blue light-emitting device or the white light emission of high color purity Equipment, described equipment be used to indicate element, display, backlight, electrofax, lighting source, Recording light source, exposure light source, read light source, signal and sign, signboard, room lighting, light is logical Letter equipment etc. The compound (1) that is used for luminaire of the present invention can be used as organic el device Material, and can be used for medical field, fluorescence-brightening agent, photographic material, UV-and absorb material The dyestuff of material, laser dye, colour filter, color conversion filter, organic semiconducting materials, Conduction organic material etc.

Claims

1, a kind of luminaire, it comprises pair of electrodes and luminescent layer and between described electrode and comprise a plurality of organic layers of a luminescent layer, described luminescent layer or comprise one deck at least in a plurality of organic layers of described luminescent layer comprise at least a below the compound of general formula (1) representative:

2, the luminaire of claim 1, wherein in described general formula (1), Ar ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵In at least one is a pyrenyl.

3, the luminaire of claim 1, wherein in described general formula (1), R ¹¹, Ar ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵In at least four be fused-aryl or condense or the heteroaryl of uncondensed.

4, the luminaire of claim 1, wherein in described general formula (1), R ¹¹, Ar ¹¹, Ar ¹², Ar ¹³, Ar ¹⁴And Ar ¹⁵In at least one is selected from naphthyl, phenanthryl, anthryl, fluoranthene base, pyrenyl He perylene base.

5, the luminaire of claim 1, the compound of wherein said general formula (1) representative is luminous by singlet excited.

6, the luminaire of claim 1, the compound of wherein said general formula (1) representative is represented by following general formula (2):

7, the luminaire of claim 6, wherein in described general formula (2), Ar ²¹, Ar ²², Ar ²³And Ar ²⁴Be selected from phenyl, naphthyl, anthryl, phenanthryl and fluoranthene base separately; Ar ²⁵Be selected from phenyl, naphthyl, anthryl, phenanthryl, fluoranthene base, pyrenyl He perylene base; R ²¹Be selected from hydrogen atom, alkyl and aryl; Ar ²¹, Ar ²², Ar ²³, Ar ²⁴And Ar ²⁵In at least one is a fused-aryl; Ar ²¹, Ar ²², Ar ²³, Ar ²⁴And Ar ²⁵Do not link to each other each other and form ring.

8, the luminaire of claim 7, wherein in described general formula (2), Ar ²¹, Ar ²², Ar ²³And Ar ²⁴Be selected from phenyl, naphthyl and phenanthryl separately.

9, the luminaire of claim 7, wherein in described general formula (2), R ²¹Be selected from hydrogen atom, phenyl and pyrenyl.

10, the luminaire of claim 6, wherein in described general formula (2), R ²¹, Ar ²¹, Ar ²², Ar ²³, Ar ²⁴And Ar ²⁵In at least four be fused-aryl or condense or the heteroaryl of uncondensed.

11, the luminaire of claim 6, wherein in described general formula (2), Ar ²¹And Ar ²²Be fused-aryl or condense or the heteroaryl of uncondensed.

12, the luminaire of claim 6, wherein in described general formula (2), Ar ²¹And Ar ²⁴Each is fused-aryl or condense or the heteroaryl of uncondensed naturally.

13, the luminaire of claim 6, wherein in described general formula (2), R ²¹, Ar ²¹, Ar ²², Ar ²³, Ar ²⁴And Ar ²⁵In at least one is selected from naphthyl, phenanthryl, anthryl, fluoranthene base, pyrenyl He perylene base.

14, the luminaire of claim 6, wherein in described general formula (2), Ar ²¹And Ar ²³Each is fused-aryl naturally, and R ²¹, Ar ²², Ar ²⁴And Ar ²⁵Be selected from phenyl, naphthyl, phenanthryl, anthryl, fluoranthene base, pyrenyl He perylene base separately.

15, the luminaire of claim 6, the described compound of wherein said general formula (2) representative is represented by following general formula (5):

16, the luminaire of claim 15, wherein in described general formula (5), Ar ⁵¹, Ar ⁵², Ar ⁵³And Ar ⁵⁴Be selected from phenyl, naphthyl, anthryl, phenanthryl and fluoranthene base separately.

17, the luminaire of claim 15, wherein in described general formula (5), R ⁵¹Be selected from hydrogen atom, alkyl and aryl.

18, the luminaire of claim 17, wherein in described general formula (5), R ⁵¹Be selected from hydrogen atom, phenyl and pyrenyl.

19, the luminaire of claim 6, the described compound of wherein said general formula (2) representative is represented by following general formula (6):

Ar wherein ⁶¹, Ar ⁶², Ar ⁶³, Ar ⁶⁴, Ar ⁶⁵, Ar ⁶⁶, Ar ⁶⁷And Ar ⁶⁸Represent aryl or heteroaryl separately; R ⁶¹And R ⁶²Represent a hydrogen atom or a substituting group separately; R ⁶³, R ⁶⁴And R ⁶⁵Represent a substituting group separately; n ⁶¹And n ⁶²Each is the integer of 0-5 naturally; n ⁶³And n ⁶⁴Represent the integer of 0-4 separately; And n ⁶⁵It is the integer of 0-8.

20, the luminaire of claim 19, wherein in described general formula (6), Ar ⁶¹, Ar ⁶², Ar ⁶³, Ar ⁶⁴, Ar ⁶⁵, Ar ⁶⁶, Ar ⁶⁷And Ar ⁶⁸Be selected from phenyl, naphthyl and phenanthryl separately.

21, the luminaire of claim 19, wherein in described general formula (6), R ⁶¹And R ⁶²Be selected from hydrogen atom, phenyl and pyrenyl separately.

22, the luminaire of claim 19, wherein in described general formula (6), n ⁶¹And n ⁶²Represent 0 or 1 separately.

23, the luminaire of claim 1, the described compound of wherein said general formula (1) representative is represented by following general formula (3):

24, the luminaire of claim 23, wherein in described general formula (3), Ar ³¹, Ar ³², Ar ³³, Ar ³⁴, Ar ³⁵, Ar ³⁶, Ar ³⁷And Ar ³⁸Be selected from phenyl, naphthyl, anthryl, phenanthryl and pyrenyl separately.

25, the luminaire of claim 1, the described compound of wherein said general formula (1) representative is represented by following general formula (4):

26, the luminaire of claim 25, wherein in described general formula (4), Ar ⁴¹, Ar ⁴², Ar ⁴³, Ar ⁴⁴, Ar ⁴⁵, Ar ⁴⁶, Ar ⁴⁷, Ar ⁴⁸, Ar ⁴⁹And Ar ⁵⁰Be selected from phenyl, naphthyl, anthryl, phenanthryl and pyrenyl separately.

27, the luminaire of claim 1, wherein the content of compound in described luminescent layer of representing as the described general formula (1) of luminescent material is 0.1-100 quality %.

28, the luminaire of claim 1 is 10-99.9 quality % as the compound of the described general formula (1) of material of main part representative at described luminescent layer or the content that comprises in a plurality of organic layers of luminescent layer at least one wherein.

29, the luminaire of claim 1, wherein said luminescent layer and comprise in a plurality of organic layers of described luminescent layer at least that one deck is a light-emitting layer.

30, the luminaire of claim 1, wherein said luminescent layer and comprise in a plurality of organic layers of described luminescent layer at least that one deck is a hole-conductive layer.

31, the luminaire of claim 1, wherein said luminescent layer comprises at least a fluorescent chemicals.

32, a kind of compound by following general formula (5) expression:

33, the compound of claim 32, wherein in described general formula (5), Ar ⁵¹, Ar ⁵², Ar ⁵³And Ar ⁵⁴Be selected from phenyl, naphthyl, anthryl, phenanthryl and fluoranthene base separately.

34, the compound of claim 32, wherein in described general formula (5), R ⁵¹Be selected from hydrogen atom, alkyl and aryl.